GB2357179A - Fluorescent colour conversion filter - Google Patents
Fluorescent colour conversion filter Download PDFInfo
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- GB2357179A GB2357179A GB0022380A GB0022380A GB2357179A GB 2357179 A GB2357179 A GB 2357179A GB 0022380 A GB0022380 A GB 0022380A GB 0022380 A GB0022380 A GB 0022380A GB 2357179 A GB2357179 A GB 2357179A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/311—Phthalocyanine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- Optics & Photonics (AREA)
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Abstract
The object of the present invention is to provide a fluorescent colour conversion film formed by a photolithography process, that suppresses degradation in colour conversion characteristic by compensating for decrease in dielectric constant due to solidification of the systems. This object is achieved by a fluorescent colour conversion film of the invention comprising an organic fluorescent dye(s) which absorbs light in a near ultraviolet to visible light region emitted from a light-emitting element and emits visible light with different wavelength, matrix resin bearing the organic fluorescent dye; and further comprises a high boiling point solvent(s) having a boiling point of 150{C or higher and a vapour pressure of 5 mmHg or lower at the temperature of 20{C.
Description
2357179 1 FLUORESCENT COLOUR CONVERSION FILM, FLUORESCENT COLOUR
CONVERSION FILTER USING THE CONVERSION FILM, AND ORGANIC LIGHT-EMITTING DEVICE EQUIPPED WITH THE CONVERSION FILTER The present invention relates to a fluorescent colour conversion film that converts light in near ultraviolet to visible region emitted by a light-emitting element to light with different wavelength in visible region. The invention also relates to a fluorescent colour conversion filter employing such a fluorescent colour conversion film and to an organic light-emitting device equipped with such a fluorescent colour conversion filter. The fluorescent colour conversion filter and the organic light-emitting device are suitably applied to both consumer-oriented and industry-used display apparatuses such as a self-emitting multicoloured- or full coloured-display, a display panel and a backlight.
With increasing demand for a flat panel display to replace a conventional CRT, development and practical application of various display devices are being actively conducted. An electroluminescent device (hereinafter referred to as a light-emitting device) is one of the devices to meet the needs. The light-emitting device has received great attention as it is a self light-emitting device of full solid-state and it exhibits such high resolution and high visibility that are not attained by other display devices.
In a known method for multicoloured or full-colored display of a light-emitting device for use in a flat panel display, light-emitting elements corresponding to three primary colours of red, blue and green are separately arranged in a matrix form and each of them is caused to emit each colour of light, as disclosed by Japanese Unexamined Patent Application Publication Nos. S57-157487, S58-147989 and H3-214593.
However, the colour display using an organic light-emitting device requires precise arrangement in a matrix form of three kinds of light-emitting material for red, blue and green. The technology for the arrangement is difficult and costly in manufacturing. In addition, the method has a problem that chromaticity gradually deviates because the lifetimes of the three light-emitting materials differ from each other.
2 In another known method for colour display, white light emitted from a backlight is passed through colour filters to obtain three primary colours, as disclosed by Japanese Unexamined Patent Application Publication Nos. 111-315988, H2-273496 and H3-194895. However, an organic white-light-emitting device exhibiting a long fife and high brightness that are necessary to attain red, green and blue light of high brightness has not been obtained yet.
In another kno,,,yn method for colour display, fluorescent elements separately arranged in a plane absorb light from a light-emitting element and each of the fluorescent elements emits fluorescent light of different colours, as disclosed by Japanese Unexamined Patent Application Publication No. H3-152897. The method in which multicoloured fluorescent light is emitted from a light-emitti,g element using fluorescent elements is also applied to CRT and plasma display.
In recent years, a colour conversion method has been developed in which fluorescent material is used as a filter, and the material absorbs light in the region of an organic light-emitting element and emits fluorescent fight in a visible light region, as disclosed by Japanese Unexamined Patent Application Publication Nos. H3-152897 and H5-258860.
In this method, colour of the light emitted from the organic light-emitting element is not limited to white light, which allows use of a brighter organic light-emitting element as a fight source. In an example of a colour conversion method using an organic light-emitting element emitting blue light, wave length conversion is performed from blue light to green or red light, as disclosed by Japanese Unexamined Patent Application Publication Nos. H3-152897, H8-286033 and H9-208944. A full-colored self-emitting display device could be constructed by precisely patterning a fluorescent colour conversion film containing such an organic fluorescent dye, even when low energy rays such as radiation in a near ultraviolet to visible light region from an organic light-emitting element would be utilized. There are following two methods among known methods for patterning a fluorescent colour conversion film.
(1) Similar to the case of inorganic fluorescent material, organic fluorescent dye is dispersed in a liquid photoresist which is a photo-reactive polymer, then, the resulting material is laminated by spin-coating, followed by patterning by means of photolithography, as 3 disclosed by Japanese Unexamined Patent Application Publication Nos.
H5-198921 and H5-258860.
(2) Fluorescent dye or fluorescent pigment is dispersed in a basic binder, then the resulting article is etched by acidic aqueous solution, as disclosed by Japanese Unexamined Patent Application Publication No.
H9-208944.
It is commonly known that a dielectric constant of a material decreases with solidification of matrix of the material. For example, methyl methaerylate, which is a monomer, has a dielectric constant of 4.0, while poly(methyl methacrylate), in which solidification has progressed by polymerization, exhibits a lowered dielectric constant down to 2.9.
Decrease in the dielectric constant due to solidification of matrix alters the environmental condition of the organic fluorescent dye, and increases ion pair interaction of the organic fluorescent dye in a ground state or an excited state, resulting in a lower value of fluorescence quantum yield of the dye. When an organic solvent of high polarity, for example, ethyl alcohol, is added to this system, the dielectric constant of the system increases, and as a result, ion pair interaction of the organic fluorescent dye is suppressed. D. A. Gromov reported in J. Opt. Soc. Am.
B/Vol. 2, No. 7, p. 1028 (1985) that addition of ethanol in Rhodamine 6G, a xanthene dye, makes an ion pair apart, which means that ion pair interaction decreases, resulting in improvement of the fluorescence quantum yield.
In forming a fluorescent colour conversion film using organic fluorescent dye dispersed in a liquid photoresist by means of photolithography process, there has been a problem that proportion of monomer decreases by polymerization due to optical or thermal curing of the resist, and the organic solvent used also evaporates, as a result, the dielectric constant of the system decreases, causing deterioration of colour conversion characteristics (fluorescence quantum yield, in particular) of the fluorescent colour conversion film.
In view of the foregoing, it is an object of the invention to provide a fluorescent colour conversion film formed by a photolithography process, that suppresses degradation in colour conversion characteristic by compensating for decrease in dielectric constant due to solidification of the system. It is another object to provide a fluorescent colour 4 conversion filter employing such a fluorescent colour conversion film. It is still another object of the invention to provide an organic light-emitting device equipped with the fluorescent colour conversion filter.
The first aspect of embodiment of the present invention is a fluorescent colour conversion film comprising an organic fluorescent dye which absorbs light in a near ultraviolet to visible light region emitted from a light-emitting-element and emits visible light of different wavelength, matrix resin bearing the organic fluorescent dye, and a high boiling point solvent having a boiling point of 15WC or higher and a vapour pressure of 5 mmHg or lower at temperature of 2WC.
The second aspect of embodiment of the present invention is a fluorescent colour conversion film as the first aspect of embodiment, wherein the high boiling point solvent is contained in an amount of 0.00001 to 50 weight % with respect to the weight of the fluorescent colour conversion film.
The third aspect of embodiment of the present invention is a fluorescent colour conversion filter comprising a fluorescent colour conversion film as the first aspect of embodiment and a substrate.
The fourth aspect of embodiment of the present invention is a fluorescent colour conversion filter as the third aspect of embodiment, wherein said high boiling point solvent is contained in an amount of 0.00001 to 50 weight % with respect to the weight of the fluorescent colour conversion film.
The fifth aspect of embodiment of the present invention is an organic light-emitting device, comprising a fluorescent colour conversion filter as third or fourth aspect of embodiment, and an organic light-emitting element.
There was a problem that a fluorescent quantum yield, which is one of colour conversion characteristics of a fluorescent colour conversion film, decreased when a system comprising organic fluorescent dye dispersed in liquid photoresist was optically or thermally cured.
That was a result of lowering of the dielectric constant of the system, which, in turn, was caused by decrease of monomers in the system due to polymerization and also caused by evaporation of the organic solvent used in the system. The inventors have found that excellent colour conversion characteristic holds when a high boiling point solvent with boiling point of 15WC or higher is added to the system.
The effect can be considered to be brought about by the following reason. The high boiling point solvent contained in the system does not evaporate by heating at a temperature of about 150'C, which is required in the fabrication process, and remains in the vicinity of the organic dye molecule. Hence, the lowering of dielectric constant of the matrix resin is prevented and the decrease of fluorescence quantum yield or quenching of fluorescence of the organic dye is suppressed.
The inventors have further found that a high boiling point solvent having a substituent(s) of greater polarity, such as a hydroxyl group or a carbonyl group better keeps the colour conversion characteristic.
The present invention has been accomplished based on the above-described findings. According to the invention, a fluorescent colour conversion film of high colour conversion efficiency is easily obtained by adding a high boiling point solvent with a boiling point of 15WC or higher and with vapour pressure of 5 mmHg or lower at 2WC to a fluorescent colour conversion film comprising an organic fluorescent dye and matrix resin bearing the organic fluorescent dye. Also, a fluorescent colour conversion filter exhibiting high precision and high colour conversion efficiency is readily obtained employing such a fluorescent colour conversion film. An organic light-ernitting device equipped with such a fluorescent colour conversion filter is also obtained. Further, for obtaining an organic light-emitting device of a specified brightness, fluorescent colour conversion filter with higher conversion efficiency according to the invention allows lower brightness of an organic light-emitting element, thus, lower driving voltage is enough to obtain the same brightness of the organic light-emitting device. The quantity of the additive high boiling point solvent is favourably controlled in the range of 0.00001 to 50 weight %, more preferably 0.00001 to 1 weight % in the fluorescent colour conversion film, depending on the species of the solvent.
6 Organic fluorescent dye used in the invention absorbs light in near ultraviolet to visible light region, in particular blue to blue- green region, and emits visible light with different wavelength. Preferably used in the invention is one or more fluorescent dye that emits at least fluorescent light in red region absorbing light in blue to blue-green region. Combination with one or more fluorescent dye emitting green light may be applied if necessary.
Among organic light-emitting elements, blue to blue-green light emitting ones are readily obtained. When light from such an element is transmitted through a red filter and converted to light in red region, however, the transmitted light becomes dark and very weak output light because the light from such an element includes essentially very little red component. Therefore, red light of sufficient intensity can be obtained only when the light from such a light-emitting element is converted to light in red region by means of organic fluorescent dye.
Light in green region may be obtained, as in the case of red light, by converting light from the fight-emitting element by means of another organic fluorescent dye. Alternatively, green light can be obtained by simply transmitting through a green filter if the light from the organic light-emitting element contains enough component of light in green region. On the other hand, light in blue region with sufficient intensity can be obtained by simply transmitting the light from an organic light-emitting element through a blue filter.
Organic fluorescent dye to be used in the invention preferably exhibits sufficient capability of fluorescence. Such fluorescent dye becomes into a singlet excited state absorbing light from a light- emitting element, and desirably exhibits low probability of the process of intersystem crossing, relaxation via oscillation, and the like, so that favourably emits fluorescent light with high quantum yield.
The organic fluorescent dye which emits fluorescent light in red region absorbing light in a blue to blue-green region emitted from a light-emitting element may be selected from a rhodamine dye such as rhodamine B, rhodamine 6G, rhodamine 3B, rhodamine 101, rhodamine 110, sulforhodamine, basic violet 11, basic red 2; a pyridine dye such as 1-ethyl-2-[4-(p-dimethylaminophenyl)-1,3-butadienyl]-pyridiniumperchlorate (pyridine 1); a cyanine dye; or an oxadine dye. Besides, various 7 dyestuffs such as direct dye, acid dye, basic dye or disperse dye may be used as far as it exhibits fluorescence.
The organic fluorescent dye which emits fluorescent light in a green region absorbing light in a blue to blue-green region emitted from a light-emitting element may be selected from a coumarin dye such as 3-(2'-benzothiazolyl)-7-diethylaminocoumarin (cournarin 6), 3-(2'-benzoimidazolyl)-7-N,N-diethylaminocoumarin (coumarin 7), 3-(2'-N-methylbenzoimidazolyl)-7-N,N-diethylaminocoumarin (coumarin 30), 2,3,5,6-1H,4H-tetrahydro-8-trffiuoromethylquinolidine(9,9a,l-gh)coumarin (cournarin 153); a dyestuff of cournarin dye species: basic yellow 51; and a naphthalimide dye such as solvent yellow 11 and solvent yellow 116.
Besides, various dyestuffs such as direct dye, acid dye, basic dye or disperse dye may be used as far as it exhibits fluorescence.
The above-listed organic fluorescent dyes may be mixed by kneading with polymethacrylate, polyvinylchloride, vinylchloride-vinylacetate copolymer resin, alkyd resin, aromatic sulphonamide resin, urea resin, melamine resin, benzoguanarnine resin, or mixture of these resins, obtaining an organic fluorescent pigment to be used in the invention. Any of these fluorescent dyes or pigments (for these two kinds of materials the term 'organic fluorescent dye' is used in the specification) may be used alone or in combination of two or more species to control a hue of the fluorescent light.
Organic fluorescent dye in the invention is contained in the fluorescent colour conversion fihn in an amount of 0.01 to 5 weight %, preferably 0.1 to 2 weight % with respect to the weight of the conversion film. If the content of the organic fluorescent dye is less than 0.01 weight %, wavelength conversion is performed insufficient. If the content is more than 5 weight %, lower efficiency of colour conversion results due to the effect of concentration quenching.
A matrix resin used in the fluorescent colour conversion Tim of the invention is a resin that is polymerized or cross-linked by radical species or ion species generated by optically treating a photo-setting resin or optically and thermally treating photo-and-thermo-setting resin to become insoluble and unmeltable. The photo-setting or photo-and-thermo-setting resin favourably is soluble to organic solvent or 8 alkaline solution before curing for facilitating patterning of the fluorescent colour conversion film. The matrix resin that may be used in the invention includes the following specific materials, for example.
(1) A material obtained by polymerization of photo-radicals or thermo-radicals which are generated by optical or thermal treatment of a film composed of acrylic multiffinctional monomer or oligomer including-a multiple of acryloyl groups or methacryloyl groups and a photo- or thermo-polymerization initiator.
(2) A material cross-finked by optically or thermally treating a composition of polyvinylcinnamate and a sensitizer.
(3) A material obtained by cross-linking olefin and nitrene, the latter is generated by optically or thermally treating a film composed of direct chain olefin or cyclic olefin and bisazide.
(4) A material polymerized by acid (cation) generation in optically or thermally treating a film composed of epoxy-group-containing monomer and acid-generating agent.
The photo-setting or photo-and-thermo-setting resin of above (1), in particular, facilitates high precision patterning and is favourable in reliability such as resistance to a solvent and resistance to heat.
A high boiling point solvent used in the invention is an organic liquid having a boiling point of 1.50'C or more. This is required for the liquid not to boil to evaporation at temperature in fabrication of the fluorescent colour conversion film. Further, a high boiling point solvent used in the invention preferably has a vapour pressure of 5 mmHg or lower at 2WC. This is because a chemical compound with high vapour pressure, for example iodine, is known to vaporize or sublimate even at temperature below boiling point in thermodynamic equilibrium. A high boiling point solvent used in the invention favourably has a large dielectric constant, and preferably contains one or more hydroxyl group or carbonyl group, or both groups. High boiling point solvents to be used in the invention include the substances represented by Formulas (P1) to (P12) listed below, but are not limited to them.
9 Chemical formula 1 HO-CH4-C--C2H4-.CH H3CO--CH4-0-C-,H4--CH -CH (P3) 02H50-C2H4--0-CH4- C4H90--C2H4-0--'c'P,4-'04 (P4) (P7) H3CO-CH2-0--C2H4--OH C$3 1 f"3C--CH--'--2H,g7-0--CH4-CH (1-9) H3C-O-C2H4-0-C-2H4-C)H (I-10) C-2--OH ( 1-1 L) 0 0 CH3 3'11 --CH 1--C-,H2--C 3 0H These high boiling point solvents can be easily synthesized by a general method or simply obtained from commercial suppliers. These solvents may be used alone or by mixing two or more solvents together.
The high boiling point solvent in the invention is contained in the fluorescent colour conversion film in the amount of from 0.00001 to 50 weight %, preferably 0.00001 to 1 weight % with respect to the weight of the conversion film.
A fluorescent colour conversion filter of the invention comprises at least the above-described fluorescent colour conversion film and a transparent substrate. Further, a fluorescent colour conversion filter of the invention may comprise a colour filter(s) or filters if necessary.
The invention will now be described with reference to the accompanying drawings, in which:
Figure 1 is a schematic cross sectional view illustrating an embodiment of a fluorescent colour conversion filter of the invention; and Figure 2 is a schematic cross sectional view illustrating an embodiment of an organic light-en.tting device of the invention.
Referring now to the Figures, Figure 1 schematically illustrates a portion corresponding to one pixel of a fluorescent colour conversion filter that has a multiple of pixels for use in multi- or full-colored display.
As shown in Figure 1, the fluorescent colour conversion filter comprises a transparent substrate 5, a red filter layer 2 laminated on the substrate, and a fluorescent colour conversion film 1 lan-dnated on the red filter layer. These layers are disposed in a predetermined plane pattern. The fluorescent colour conversion film 1 comprises one or more organic fluorescent dyes, one or more high boiling point solvents including those represented by Formulas (P1) to (P12), which are not limited to them, and matrix resin obtained by hardening photo-setting resin or photo-and-thermo-setting resin. The red filter layer 2 transmits red light converted by the fluorescent colour conversion film 1 and cuts off light in other colours.
A green filter layer 3 and a blue filter layer 4 are also formed on the transparent substrate 5 in each predetermined pattern. Each of these filters transmits only green light or blue light out of the light emitted from the organic light-emitting element and outputs light in each 11 colour. Protective film 6 and insulative inorganic oxide film 7 cover the filter layers and constitute together a fluorescent colour conversion filter.
While the fluorescent colour conversion filter illustrated in Figure 1 emits green fight using only green filter layer 3, a fluorescent colour conversion film for green colour may be provided on the green filter layer 3, if required.
It is desired that the substrate suitably used in the invention is transparent to visible light and dimensions thereof are stable. The materials appropriate for the substrate include glass, quartz, sapphire and polymer such as polyimide, but are not limited to them.
The fluorescent colour conversion film of the invention may be formed by coating on an appropriate substrate according to a method known in the art, such as spin-coating, casting or dip-coating. The coating is performed using a solution or a dispersion liquid containing organic fluorescent dye, high boiling point solvent, and a component for forming matrix resin. Thickness of the fluorescent colour conversion film is preferably in the range from 0.1 to 50 gm, more preferably from 1.0 to 10,um, depending on content of the organic fluorescent dye.
Patteming of the fluorescent colour conversion film can be conducted by means of photoEthography.
Colour filters that may be employed in the fluorescent colour conversion filter of the invention are used for adjusting hues of output light of an organic light-emitting device of the invention. For adjusting a hue of the light undergone wavelength conversion by the fluorescent colour conversion film, a colour filter is disposed between the colour conversion film and the substrate. A colour filter may be disposed in the portion without fluorescent colour conversion film on the substrate, and a hue of the light from the light-emitting element can be adjusted. A colour filter can be fabricated employing commonly used or commercially available material.
The fluorescent colour conversion filter may further comprise a protective layer and an insulative oxide layer, as required.
A protective layer which may be comprised by the fluorescent colour conversion filter of the invention is favourably formed covering the fluorescent colour conversion film and protects the conversion film 12 from oxygen and other harmful material. The surface of the protective layer in the opposite side to the substrate is favourably flat because an organic light-emitting element is formed on the surface. The protective layer may be formed using commonly used resin and employing commonly practised coating method. The protective layer preferably_ is transparent to visible light.
An insulative inorganic oxide film that may be comprised by the fluorescent colour conversion filter of the invention is disposed preferably on a protective layer having a flat surface. The insulative inorganic oxide film can be formed by a commonly used method, such as, vacuum deposition, sputtering, or CVD. The oxide film also preferably is transparent to visible light. Si02 is a favourable material as the oxide film.
A fluorescent colour conversion filter of the invention also may be used as a backlight when the conversion filter comprises at least a transparent substrate, a colour filter on the substrate as required, and a fluorescent colour conversion film uniformly formed on the whole surface of the substrate. Alternatively, a fluorescent colour conversion filter may be used as a display device when the conversion filter comprises at least a transparent substrate, a colour conversion film(s) formed only at desired portion on the substrate.
An organic light-emitting device of the invention comprises the fluorescent colour conversion filter described above and an organic light-emitting element. The fluorescent colour conversion filter absorbs light in a near ultraviolet to visible light region, preferably in a blue to blue-green region, emitted from the organic light-emitting element and emits visible Eght of different wavelength.
The organic light-emitting element has a structure in which an organic light-emitting layer is sandwiched between a pair of electrodes and, as required, a hole injection layer and an electron injection layer are interposed. The following layer constructions may be applied:
(1) anode / organic light-emitting layer / cathode (2) anode hole injection layer / organic light-emitting layer / cathode (3) anode organic light-emitting layer / electron injection layer / cathode (4) anode hole injection layer / organic light-emitting layer electron injection layer / cathode (5) anode / hole injection layer / hole transport layer organic light-emitting layer / electron injection layer / cathode 13 In the above structure, at least one of the anode and cathode is favourably transparent to the wavelength range of the light emitted from the organic light-emitting element, which radiates light through the transparent electrode into the fluorescent colour conversion film. It is known in the art that obtaining transparent anode is easier. A transparent anode is preferably employed also in the invention.
Material of each of the above layers may be selected from known substances. For the material of the organic light-emitting layer to obtain blue to green light, a fluorescent brightening agent such as benzothiazole, benzimidazole or benzoxazole, a metal chelate oxonium compound, a styrylbenzene compound, or an aromatic dimethylidyne compound may be favourably used.
Figure 2 is a schematic cross sectional view of the whole structure of an organic light-emitting device. Figure 2 schematically illustrates a portion corresponding to one pixel of an organic light-emitting device that has a multiple of pixels for use in multi- or full-colored display.
An organic light-emitting element is formed on the fluorescent colour conversion filter, as shown in Figure 2. The organic light-emitting element comprises an anode 8 composed of transparent electrodes of ITO, for example, patterned on the insulative inorganic oxide film 7, a hole injection layer 9 covering the anode 8, a hole transport layer 10 formed on the hole injection layer 9, an organic light-emitting layer 11 formed on the hole transport layer 10, an electron injection layer 12 formed on the organic fight-emitting layer 11, and a cathode 13 composed of metal electrodes patterned on the electron injection layer 12.
The patterns of the anode 8 and the cathode 13 in the invention may be formed in each set of parallel stripes and the two sets of stripes are disposed orthogonal with each other. In that disposition, the organic light-emitting device of the invention can be matrix driven. That is, when selected stripes of the anode 8 and selected stripes of the cathode 13 are electrically charged, the organic light-emitting layer 11 emits light at the positions where the charged stripes cross each other.
14 Therefore, only the points in the light-emitting layer where a specific filter layer or a specific combined layer of a filter and a fluorescent colour conversion film disposes can be lit by charging a selected set of anode stripes and a selected set of cathode stripes. The light from the selected points transmits through each of the filter layers or thecombined layers of a filter and a fluorescent colour conversion film, and each of the selected colours is output through the transparent substrate 5. For example, the-red light emitting portion 21 which corresponds to the fluorescent colour conversion film 1 is lit, then, the light is converted to red light in the fluorescent conversion film 1, goes through the red filter layer 2 and the transparent substrate 5, and output as a red light. In case the green light emitting portion 22 which corresponds to the green filter layer 3 are lit, the light after transmission through the green filter layer changes to light including only green component and output through transparent substrate 5. Similarly, if the blue light emitting portion 23 which corresponds to the blue filter layer 4 are lit, the light after transmission through the blue filter layer changes to light including only blue component and output through transparent substrate 5.
Alternatively, in an invented organic light-emitting device, anode 8 may be a uniform flat electrode, and cathode may be patterned corresponding to the pixel array. In that construction, so-called active matrix drive is possible by providing switching elements corresponding to the pixel array.
Alternatively, both of the anode and cathode may be formed totally uniform in an organic light-emitting device of the invention.
Such a device can be used as a backlight.
(Example 1)
The filter portion illustrated in Figure 1 is fabricated by the process described below.
A transparent substrate 5 of coming glass (143 x 112 x 1.1 mm) was prepared. Colour filter red (available under the trade name Colormosaic CR-7001 from Fuji Film Olin Co., Ltd.) was coated by means of spin-coating on the substrate, followed by patterning by photolithography, to obtain a red filter layer having a stripe pattern of I gm thickness, 0.104 mm width and 0.226 mm gap.
Similarly, each of colour filter blue (available under the trade name Colormosaic CB-7001 from Fuji Film Olin Co., Ltd.) and colour filter green (available under the trade name Colormosaic CG-7001 from Fuji Film Olin Co., Ltd.) was coated by means of spin-coating on the substrate, followed by patt erning by photolithography, to obtain each of a blue filter layer 4 and a green filter layer 3 each having a stripe pattern of 1 gm thickness, 0.104 mm width and 0.226 mm gap.
As the organic fluorescent dyes, 0.6 parts by weight of coumarin 6, 0.3 parts by weight of rhodamine 6G and 0.3 parts by weight of basic violet 11 were used. The mixture of the dyes and 10 parts by weight of diethylene glycol, a high boiling point solvent represented by formula (P1) were dissolved in 50 parts by weight of propylene glycol monoethyl acetate (PGMEA). To the obtained solution, 100 parts by weight of a transparent photopolymerizing resin, V-259PA/P5 (a. trade name) from Nippon Steel Chemical Co. Ltd., was added and dissolved to obtain a coating solution. The coating solution was coated on the surface of the filter layers by spin-coating followed by baking in an oven at WC to obtain a fluorescent colour conversion film. Polyvinylalcohol was coated on the fluorescent colour conversion film by spin-coating and dried to form an oxygen isolating film (not shown). Tle obtained laminate was exposed through a mask using an exposure apparatus equipped with a light source of a high pressure mercury lamp to be patterned with stripes of 0.104 min width and 0.226 mm gap, and washed by pure water, followed by development with alkaline aqueous solution to form a fluorescent colour conversion film 1 with a stripe pattern on the red filter layer 2. Then, the resulted article was baked in an oven at 16WC to obtain a fluorescent colour conversion filter of maximum thickness 7 gm including filter layers 2, 3 and 4 for three colours of 1 urn thick and a fluorescent conversion filter layer 1 of 6 gm thick on the red filter layer.
UV hardening type resin, which is epoxy modified acrylate, was coated on the thus obtained fluorescent colour conversion filter by spin-coating, and exposed by a high pressure mercury lamp to form a protective layer 6. The protective layer 6 had a thickness of 3 gm above the colour conversion film and the top surface thereof was flat. The pattern of the fluorescent colour conversion filter 1 was not distorted.
A heating test at 1OWC was conducted, and any distortion of the 16 fluorescent colour conversion filter 1 or the protective layer 6 was not observed. An insulative inorganic oxide film 7 was formed on the whole surface of the protective layer by depositing 300 nm Of Si02 film by means of sputtering.
On the fluorescent colour conversion filter fabricated as described above, an organic light-emitting element was formed having 6 layer structure of anode 8 / hole injection layer 9 / hole transport layer / organic light-emitting layer 11 / electron injection layer 12 cathode 13, as shown in Figure 2.
First, a film for transparent electrodes (ITO) was formed by sputtering method on the whole surface of insulative inorganic oxide film 7, which is an outermost layer of the fluorescent colour conversion filter. Then, photoresist (available under the trade name OFRP-800 from Tokyo Ohka Kogyo Co., Ltd.) was coated on the ITO, followed by patterning by means of photolithography to obtain anode 8 constituting patterns of stripes disposed at each of the light-emitting portions for red 21, green 22, and blue 23, the stripes having a width of 0.094 mm, a gap of 0.016 mm and a film thickness of 100 nm.
After that, the resulting substrate having the anode was installed in a resistance-heating evaporation chamber, and hole injection layer 9, hole transport layer 10, organic light-emitting layer 11 and electron injection layer 12 were successively deposited in the same chamber holding a vacuum. Table I shows the substances and their structural formulas used in these layers. The pressure in the evaporation chamber during deposition process was 1 x 10-4 Pa. Hole injection layer 9 was formed by depositing 100 nm of Cu phthalocyanine (CuPc). Hole transport layer 10 was formed by depositing 20 nm of 4,4'-bis[N-(l-naphthyl)-N-phenylamino] biphenyl (a-NPD). Organic light-emitting layer 11 was formed by depositing 30 nm of 4,4'-bis(2,2'-diphenylvinyl) biphenyl (DPVBi). Electron injection layer 12 was formed by depositing 20 nm of tris(8-quinolinolato)aluminum (Alq).
17 Table 1 laver subetance structural formula hole inje&.jon Cu phthalocyanine 7 1 \, layer N-P-- N N N N N.
hole transcort 4,4'-bis[N--/,.1-naphthyi) layer N--phenyiamincl biphenyi N li&,-cr,nitbng 4,4'-bis(2,2-diphenyivinyi) layer biphenyi electron injection +ms(8-quinoiinoiato) layer 1 aluminium 1 A-1:
12 0 18 Then, the substrate 5 with the laminate thereon was taken out from the evaporation chamber. After being attached a mask for patterning stripes of cathode orthogonally arranged with respect to lines of anode (ITO), the substrate was again installed into the resistance-heating evaporation chamber to obtain a cathode having the pattern of stripes each having -a width of 0.30 mm and a gap of 0.03 mm. The cathode was formed of a Mg-Ag (weight ratio 10:1) layer having a thickness of 200 nm.
Thus obtained organic light-emitting device was sealed with a sealing glass plate (not shown) and UV-hardening adhesive under a dry nitrogen atmosphere in a glove box.
The organic light-emitting element in the organic light-emitting device fabricated as described above emits blue-green light with wavelength in the range of 430 to 550 nm.
(Example 2)
A fluorescent colour conversion filter of Example 2 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (I-1) of Example 1 was replaced by 10 parts by weight of diethylene glycol monomethyl ether of Formula (1-2), and an organic light-emitting device of Example 2 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
(Example 3)
A fluorescent colour conversion filter of Example 3 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (1-1) of Example 1 was replaced by 10 parts by weight of diethylene glycol monoethyl ether of Formula (1-3), and an organic light-emitting device of Example 3 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
(Example 4
A fluorescent colour conversion filter of Example 4 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (1-1) of Example 1 was replaced by 10 parts by weight of 2-benzyloxyethanol of Formula (1-5), and an organic light-emitting device of Example 4 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
19 (Example 51
A fluorescent colour conversion filter of Example 5 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (P1) of Example 1 was replaced by 10 parts by weight of diacetone alcohol of Formula (P12), and an organic light-emitting device of Example 5 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
(Comparative Examl2lel) A fluorescent colour conversion filter of Comparative Example 1 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (P1) of Example 1 was not used, and an organic light-emitting device of Comparative Example 1 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
(Comparative Example!) A fluorescent colour conversion filter of Comparative Example 2 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (P1) of Example 1 was replaced by 10 parts by weight of acetone, and an organic light-emitting device of Comparative Example 2 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
(Comparative Example---j) A fluorescent colour conversion filter of Comparative Example 3 was fabricated repeating the same process as in Example 1 except that 10 parts by weight of diethylene glycol of Formula (M) of Example 1 was replaced by 10 parts by weight of methanol, and an organic light-emitting device of Comparative Example 3 equipped with thus fabricated fluorescent colour conversion filter was fabricated.
The organic light-emitting devices of Examples 1 through 5 and Comparative Examples 1 through 3 were evaluated on the red light emitting portion of each of the organic light-emitting devices. The results are summarized in Table 2. The methods and results of the evaluations of the items in Table 2 are described in the following:
Table 2
CIE chromaticity relative high botlingpoint solvent coordinate conversion X i Y efficiency Example i J_diglhyiene glycol 0.65 0.34 1.33 Example 2 diethyiene glycol 0-64 monomethyl ether Example 3 diethylene glycol 0.65 0.34 1.02 monoethyl ether 0.6S 1-01 Example 4 2--benzyloxyethanol -1 _ 1 diacetOne alcohol 0. 6 5 0.33 1 0.98 Examoie 5 Compative Examp c no c 0.61 0.36 0.88 Comr)ative Exampie 2 acetone 0.60 0.36 1 0.87 _f-amoative Example 3 rne:hanoi 0.62 -0.35 0.89 CIE chromaticity coordinate was measured with "MCPD-1000" (a trade name) manufactured by Ohtsuka Denshi Co., Ltd. - Relative conversion efficiency is defined as brightness of a sample of an organic light-emitting device lit by applying a standard voltage relative to brightness of Example 1 lit by the standard voltage.
The standard voltage is determined as the voltage that brings about brightness of 50 cd/m' with the organic light-emitting device of Example 1.
Clearly, red light emission with high colour purity and high relative conversion efficiency were achieved in Examples 1 through 5 where the high boiling point solvents with boiling points of 15WC or higher were used. In contrast, lower red colour purity and degraded relative conversion efficiency resulted with Comparative Example 1 where no high boiling point solvent was added and with Comparative Examples 2 and 3 where acetone or methanol having boiling point lower than 150,C was added.
As explained in the foregoing, the present invention provides a fluorescent colour conversion film which absorbs light in a near ultraviolet to visible light region from a light-emitting element and converts to visible light with different wavelength, for example, red light. The fluorescent colour conversion film of the invention comprises a high boiling point solvent(s) to prevent lowering of fluorescent quantum yield, bringing about excellent colour conversion characteristics. By employing such a fluorescent colour conversion film, a fluorescent colour - conversion filter capable of highly precise patterning can be easily 21 obtained with low cost. In addition, an organic light-emitting device equipped with such a fluorescent colour conversion filter may be suitably applied to commercial-oriented and industry-used display apparatuses, such as a self-lightening multicoloured or full-colored display, a display panel, and a backlight. Moreover, a full-colored display device with organic light-emitting elements capable of low voltage driving can be manufactured by equipment of the fluorescent colour conversion filter of the invention. - 22
Claims (5)
1. A fluorescent colour conversion film, comprising:
at least one organic fluorescent dye which absorbs light in a near ultraviolet to visible light region emitted from a light-emitting element and emits visible light of different wavelength; at least one matrix resin bearing said organic fluorescent dye; and at least one high boiling point solvent having a boiling point of 150T or higher and a vapour pressure of 5 mmHg or lower at temperature of 20T.
2. A fluorescent colour conversion film as claimed in claim 1, wherein said high boiling point solvent is contained in an amount of 0.00001 to 50 weight % with respect to the weight of said fluorescent colour conversion film.
3. A fluorescent colour conversion filter, comprising:
a fluorescent colour conversion film including at least one organic fluorescent dye which absorbs light in a near ultraviolet to visible light region emitted from a light-emitting element and emits visible light of different wavelength, at least one matrix resin bearing said organic fluorescent dye, and at least one high boiling point solvent having a boiling point of 150T or higher and a vapour pressure of 5 mmEg or lower at temperature of 20T; and a substrate.
4. A fluorescent colour conversion filter as claimed in claim 3, wherein said high boiling point solvent is contained in an amount of 0.00001 to 50 weight % with respect to the weight of said fluorescent colour conversion film.
5. An organic light-emitting device, comprising:
a fluorescent colour conversion filter including a fluorescent colour conversion film containing at least one organic fluorescent dye which absorbs light in a near ultraviolet to visible light region emitted from a light-emitting element and emits visible light of different wavelength, at least one matrix resin bearing said organic fluorescent dye, and at least one high boiling point solvent having a boiling point of 15TC 23 or higher and a vapour pressure of 5 mmHg or lower at temperature of 20'C, and a substrate; and an organic light-emitting element.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27129899A JP3463866B2 (en) | 1999-09-24 | 1999-09-24 | Fluorescent color conversion film, fluorescent color conversion filter using the same, and organic light emitting device including the fluorescent color conversion filter |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB0022380D0 GB0022380D0 (en) | 2000-11-01 |
| GB2357179A true GB2357179A (en) | 2001-06-13 |
| GB2357179B GB2357179B (en) | 2003-09-10 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0022380A Expired - Fee Related GB2357179B (en) | 1999-09-24 | 2000-09-13 | Florescent colour conversion film |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US6653778B1 (en) |
| JP (1) | JP3463866B2 (en) |
| GB (1) | GB2357179B (en) |
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| GB2412662A (en) * | 2004-04-01 | 2005-10-05 | Fuji Electric Holdings | Method of manufacturing color-converting filter |
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Also Published As
| Publication number | Publication date |
|---|---|
| GB2357179B (en) | 2003-09-10 |
| GB0022380D0 (en) | 2000-11-01 |
| JP3463866B2 (en) | 2003-11-05 |
| US6653778B1 (en) | 2003-11-25 |
| JP2001093669A (en) | 2001-04-06 |
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